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I just read a post by Ben Pieratt, the CEO of Svpply, a social shopping site from New York City.

Ben recently raised $500,000 dollars in investment, and he admits to having very little understanding of what he is doing.

As he says: "I have zero experience or expertise in building a company. I’ve never worked at a web or product startup, I’ve never worked in a healthy team environment."

Ben ends his post with a description that will sound eerily familiar to any founder in a similar position: "My level of personal confidence is appropriate. Skeptically hopeful. The bouts of depression and self-doubt are reasonable and inevitable….I couldn’t ask for better. I am thankful for the opportunity. It is an amazing challenge."

When I dropped out of law school to found WePay in the Fall of 2008, I had this notion of what it was like to start a company: You come up with a great idea, convince investors to give you money to build it, hire people to build it, and watch as the customers and dollars role in.

While I was obviously incredibly naive, I owe everything to that initial naiveté: without it, I never would have had the courage and resolution to venture off the beaten path, alone and in the dark.

In the beginning, my co-founder (Bill Clerico) and I spent a year trying, unsuccessfully, to raise money during "the worst recession since the Great Depression," and it cost us nearly a year of our lives and hundreds of thousands of dollars in opportunity.

It was like getting punched in the face repeatedly, and I am embarrassed to admit how close I was to crawling back to law school, tail between legs. It was my first major bout of self-doubt and uncertainty; not only in regard to WePay, but in my entire life.

Tim Ferris writes about Harnessing Entrepreneurial Manic-Depression. In it, he outlines the general path of the entrepreneur psyche: At some point, we trade the excitement of uninformed and unmitigated optimism for the anxiety and depression of informed pessimism.

This happens when we go from "I have the next million dollar idea!" to "Holy s--t, this is going to be a lot harder than I thought, and I'm not so sure that I can pull it off."

We enter the "Crisis of Meaning," or what Paul Graham calls the "Trough of Sorrow". This is where fear of failure becomes one's greatest asset: sometimes it's the only thing between stopping you from giving up. It certainly was for my co-founder and me.

Most first-time founders enter the Trough of Sorrow when they realize that launching a product is the starting point, not the finish line. It seems obvious now, but I remember how scary and depressing it was at the time.

After months of obsessing, building, and making assumptions about how people will use your product, and how easily it will be to grow your business, you're rewarded with the harsh and unsympathetic feedback of reality: Nobody cares about what you have built. You realize that you could have built a machine that turns water into gold, given it away for free, and you still would have needed to beg, barter, and steal to get the first thousand people to use it.

Since then, we have had a few successful strategies for acquiring customers, but every one of them has been a difficult, uphill battle, carefully planned, and well-executed.

Whenever new founders ask me for advice, they always start by telling me about their "great idea." Some of the more naive ones ask me to sign an NDA or ask me to keep their idea confidential. Then they frenetically describe what they are going to build, often in painful detail - all the features, the future possibilities, the business models, etc.

The implicit assumption is that building this thing is the challenge, and watching it grow is the reward.

Uninformed optimism at its finest; the crash, inevitable.

I always try to prepare founder friends for the uncertainty, doubt and sorrow that assuredly awaits them. But they never hear me. I started quoting a great line from the movie Frost/Nixon: “In boxing, there’s always that first moment, and you see it in the challenger’s face. It’s that moment that he feels the impact from the champ’s first jab. It’s kind of a sickening moment, when he realizes that all those months of pep talks and the hype, the psyching yourself up, had been delusional all along.”

I'm usually interrupted halfway, before I even get to the punchline, by the founder's second gushing description of all the functionality he failed to mention the first time.

You see, it’s one thing to know how strong the champ can hit, and something quite different to feel it.

That’s kind of what it’s like to start a company: we think we're ready for the roller-coaster. And then we feel that first punch. Every newfounder is surprised by it, at least once and sometimes daily. The life of a founder is dark and uncertain, and only the lucky ones make it out alive.

At the time, you beat yourself up for the naivete and decisions that have led you to this latest crisis. You doubt whether you're the right person for the job.

But, as Steve says, “You have to trust that the dots will somehow connect in your future."

When you're in it, your Trough of Sorrow feels unique and insurmountable. And then you realize: it's an inevitable part of the game, and every founder must find a way to claw their way out. Looking back, you're grateful that things happened just the way that they did.

It's not for everybody, but I wouldn't trade it for anything in the world.